WO2017111711A1 - Composition à base de polymère anti-salissure - Google Patents

Composition à base de polymère anti-salissure Download PDF

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Publication number
WO2017111711A1
WO2017111711A1 PCT/TH2016/000104 TH2016000104W WO2017111711A1 WO 2017111711 A1 WO2017111711 A1 WO 2017111711A1 TH 2016000104 W TH2016000104 W TH 2016000104W WO 2017111711 A1 WO2017111711 A1 WO 2017111711A1
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WO
WIPO (PCT)
Prior art keywords
polyethylene
parts
antifouling
weight
polymer based
Prior art date
Application number
PCT/TH2016/000104
Other languages
English (en)
Inventor
Nopphawan Phonthammachai
Wareerom POLRUT
Noppakun SANPO
Original Assignee
Scg Chemicals Company Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from TH1501007806A external-priority patent/TH167832A/th
Application filed by Scg Chemicals Company Limited filed Critical Scg Chemicals Company Limited
Publication of WO2017111711A1 publication Critical patent/WO2017111711A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/015—Biocides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0058—Biocides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/378—Thiols containing heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • C08K5/47—Thiazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/02—Ingredients treated with inorganic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2296—Oxides; Hydroxides of metals of zinc
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/321—Phosphates
    • C08K2003/325—Calcium, strontium or barium phosphate

Definitions

  • polyolefin has been used for various applications such as for producing packages, tubes, films, etc.
  • polyolefin cannot be applied for certain applications e.g. underwater pipes, roto-molding products for submarine applications, polymer based coatings, etc.
  • a number of efforts has been made to invent and develop polyolefin polymer based products capable of preventing fouling caused by aquatic organisms, for example, by coating the polymer surface with particles having such antifouling properties by e.g. heat spray coating.
  • such coating method is not suitable for producing products for submarine applications due to the leaching of the antifouling particles. Examples of such efforts to invent and develop self-antifouling polymer based compositions are shown by the following prior arts.
  • US 6,635,692 Bl discloses an antifouling polymer based composition
  • polymer is selected from a group consisting of ethylene-vinyl acetate copolymer (EVA), high density polyethylene (HDPE), sodium ionomer, copolymer of ethylene and acrylic acid and mixtures thereof
  • organic agent is selected from a group consisting o isothiazolone based agent (e.g.
  • UHMWPE ultra high molecular weight polyethylene
  • US 5.916,947 discloses an antifouling coating composition
  • an antifouling coating composition comprising zinc oxide which is coated with photosensitizer to increase the capability of zinc oxide to absorb visible light.
  • Said coating composition having 20 to 60 wt% of zinc oxide and said photosensitizer is selected from a group consisting of fumed anatase, strontium titanate, bianthrone, azulene, zinc pyrithione, terthiophene, hypericin and mixtures thereof.
  • Said coating further comprises additional polymers e.g. polyvinyl, polyalkyd, polyepoxide, polysiloxane, polyurethane, polyacrylonitrile, polyacrylate, polyester resin or mixtures thereof.
  • the present invention relates to a self-antifouling polyolefin based composite composition.
  • the present invention relates particularly to an antifouling polymer based composition
  • an antifouling polymer based composition comprising polyethylene (PE) and at least one antifouling-active filler selected from the group consisting of 2-methylthio-4-ethylamino-6-tert-butylamino-s-triazine, 2,4,4'-trichloro-2'- hydroxy diphenyl ether, 2-benzisothiazol-3-one, zinc oxide, bis(2-pyridylthio)zinc 1 ,1 '- dioxide, metal -doped hydroxyapatite, copper-containing chitosan and mixtures thereof, wherein the antifouling-active filler is present in a range of 0.1-5 parts by weight based on 100 parts by weight of polyethylene.
  • PE polyethylene
  • antifouling-active filler selected from the group consisting of 2-methylthio-4-ethylamino-6-tert-butylamino-s-triazine
  • the object of the present invention is to provide an antifouling polymer based composition capable of preventing fouling caused by aquatic organisms e.g. algae, barnacles, etc.
  • the composition offers technical advantages resulting from good dispersion and distribution of the antifouling-active filler in a polymer matrix, high stability due to the antifouling-active filler according to the present invention still remaining highly stable after mixing with the polymer, low leaching rate o the antifouling-active filler of the polymer based composition from the polymer matrix, environmental-friendly, long service life, and persistent mechanical properties of the polymer or the plastic products, etc.
  • Fig. 1 shows the microstructure (rnicrostructure) of the cross-sectional surface of the polymer based composition according to the present invention.
  • Fig. 2 is a graph showing the relationship between the antifouling-active fillers and the mechanical properties of the polymer based compositions.
  • Fig. 3 shows the antibacterial test: (a) the antibacterial property against S. aureus cultured by agar diffusion method; (b) a graph showing the relationship between the inhibition zone for S. aureus and the types of antifouling-active filler in the polymer based composition.
  • Fig. 4 shows the antibacterial test: (a) antibacterial property against S. aureus cultured by broth dilution method; (b) a graph showing the relationship between the amount of S. aureus in the broth solution and types of the antifouling-active fillers in the polymer based compositions.
  • Fig. 5 shows the antibacterial test: (a) antibacterial property against E. coli cultured by agar diffusion method; (b) a graph showing the relationship between the inhibition zone for E. coli and types of antifoul ing-active filler in the polymer based compositions.
  • Fig. 6 shows the antibacterial test: (a) antibacterial property against E. coli cultured by broth dilution method; (b) a graph showing the relationship between the amount of E. coli in the broth solution and types of the antifouling-active fillers in the polymer based compositions.
  • Fig. 7 shows fouling profile of marine organisms on the sample polymer sheets.
  • the antifouling polymer based composition according to the present invention comprises: polyethylene (PE) selected from low density polyethylene (LDPE), linear low density polyethylene (LLDPE), high density polyethylene (HDPE) or mixtures thereof; and at least one antifouling-active filler selected from a group consisting of 2-methylthio-4- ethylamino-6-tert-butylamino-s-triazine, 2,4,4 ' -trichloro-2 ' -hydroxy diphenyl ether, 2- benzisothiazol-3-one, zinc oxide, bis(2-pyridilthio)zinc 1 ,1 '-dioxide or zinc pyrithione, metal- doped hydroxyapatite, copper-containing chitosan and mixtures thereof.
  • the antifouling-active filler is present in a range of
  • the antifouling-active filler is preferably present in a range of 0.1- 3 parts by weight based on 100 parts by weight of polyethylene.
  • the antifouling-active filler according to the present invention is an antifouling-active filler acting against fouling caused by algae, barnacles, etc.
  • polyethylene preferably has a density in a range of 0.95- 0.98 g/cm 3 and has a flow index in a range of 0.25 -0.50 g/10 minutes.
  • the metal -doped hydroxyapatite herein is hydroxyapatite with added metal which is selected from a group consisting of Ag-doped hydroxyapatite (Ag-doped hydroxyapatite), Ni-doped hydroxyapatite (Ni-doped hydroxyapatite) and mixtures thereof.
  • the antifouling polymer based composition may further comprise a polymer additives including a lubricant facilitating good mixing and acid scavenger neutralizing catalyst residue in the polymer as well as antioxidant in order to prevent polymer degradation from oxidation reaction of the polymer containing said antifouling-active filler. This would lengthen the service life time of the product and prevent the yellowing of the product during the molding process.
  • the additive according to the present invention is selected from a group consisting of calcium stearate, zinc stearate, antioxidant and mixtures thereof. According to the present invention, said additive may be present in the polymer based composition in a range of 0.1 -5 parts by weight based on 100 parts by weight of polyethylene.
  • antioxidants in case of primary antioxidant or phenolic antioxidant.
  • primary antioxidants are pentaerythritol tetrakis (3-(3,5-di-tert-butyl- 4-hydroxyphenyl)propionate), etc.
  • secondary antioxidant or peroxide decomposers examples of secondary antioxidant are tris(2,4-di-tert-butylphenyl)phosphite, etc.
  • the antioxidant according to the present invention is selected from a group consisting of tetrakis[methylene(3,5-di-tert-butyl-4-hydroxy)hydrocinnamatejmethane, tris(2,4-di-tert- butylphenyl)phosphite and mixtures thereof. Said antioxidant is present in a range of 0.1 -5 parts by weight based on 100 parts by weight of polyethylene.
  • the antifouling polymer based composition may further comprise at least one polymer selected from the group consisting of poly(methyI methacrylate) (PMMA), polypropylene (PP), polyurethane (PU), melamine (melamine), polyvinyl chloride (PVC) and mixtures thereof in a range of 5-30 parts by weight based on 100 parts by weight of polyethylene.
  • PMMA poly(methyI methacrylate)
  • PP polypropylene
  • PU polyurethane
  • melamine melamine
  • PVC polyvinyl chloride
  • the term "antifouling” as described above is not limited only to preventing the fouling caused by algae and/or barnacles but also microorganism such as microbes, bacteria or macroorganism which is involved in or cause algae and/or barnacle fouling.
  • said antifouling polymer based composition can be molded into a variety of products, for example, submarine pipe for transferring oil or gas.
  • the antifouling polymer based composition according to the present invention can be prepared by mixing polyethylene e.g. high density polyethylene with 3 wt% of anti ouling- active filler, and other additives may be added. The mixing is carried out using a high speed mixer to obtain the polymer based composition in the form of homogenous powder. The obtained product is then subjected to extrusion process in a twin screw extruder under a condition which homogenous plastic pellet can be obtained. Samples of the polymer based compositions prepared by mixing with each of the antifouling-active additives are
  • Z a polymer based composition having zinc oxide
  • Zl is a polymer based composition having nanoparticle zinc oxide
  • Z2 is a polymer based composition having microparticle zinc oxide
  • ZP a polymer based composition having bis(2-pyridilthio)zinc 1 , 1 '-dioxide or zinc pyrithione, herein abbreviated as ZP;
  • melt flow index as carried out by melting plastic pellet in a cylinder at a determined temperature then applying weight on the piston allowing the piston to act on the melted plastic in the cylinder, making the melted plastic flo out of the die head. The flown-out plastic is then weighed for 10 minutes to determine the flow rate of the melted plastic in gram per 10 minutes.
  • melt flow index and mechanical properties refer to the viscosity, the molecular weight and the mechanical strength of the polymer based compositions containing each of the antifouling-active fillers.
  • the antibacterial test of the polymer based composition comprising each of the antifouling-active filler according to the present invention was carried out using 2 types of general bacteria which are not severely harmful to living organisms and easy to use for the test i.e. Staphylococcus aureus (S. aureus) representing gram positive bacteria and Escherichia coli (E. coli) representing gram positive bacteria.
  • the test has 2 following sections.
  • Section 1 Agar diffusion method— the test was carried out by placing a fixed volume of circular specimen on the agar having a concentration of 1.5 to 2 wt% on which the bacteria was cultured. If the filler is capable of inhibiting the growth of the test bacteria, an inhibition zone or a clear zone will appear. The bigger the clear zone is, the greater the inhibition efficiency will be. This method can be carried out easily, conveniently and fast and allows testing multiple substances at the same time. This method is suitable for bacteria taking 18-24 hr of incubation.
  • Section 2 Broth dilution method was used for confirming the result from agar diffusion method. This test was carried out by conducting two-fold serial dilution to obtain diluted solutions with different bacteria concentrations. The obtained diluted solutions were adjusted to achieve 0.5 turbidity (McFarland standard), then incubated at 37°C for 24 hours. The results were read by observing the growth of the test bacteria based on the turbidity present. If bacterial inhibiting plastic specimen has great efficiency, no turbidity will appear in the test samples.
  • Fig. 3(a) shows that the polymer based composition comprising the antifouling-active filler according to the present invention were capable of significantly inhibiting the growth of S. aureus.
  • the polymer based composition comprising the antifouling-active filler, 2-benzisothiazol-3-one (2 BO) and copper-containing chitosan (CCu) shows the biggest clear zone having the average diameter of 5.5 cm as shown in Fig. 3(b).
  • the polymer based composition comprising the antifouling-active filler according to the present invention is capable of significantly inhibiting the growth of bacteria in the broth solution. Furthermore, the results from a quantitative analysis carried out by measuring the turbidity of the test solutions using UV visible spectroscopy at the wavelength of 600 run as shown in Fig. 4(b). In conclusion, the polymer based composition comprising the antifouling-active filler according to the present invention is capable of significantly inhibiting the growth of the bacteria in the broth solution.
  • the polymer based composition comprising the antifouling-active filler according to the present invention is capable of significantly inhibiting the growth of E. coli.
  • the polymer based composition comprising the antifouling-active filler of copper-containing chitosan (CCu) shows the biggest clear zone of an average diameter of 5 cm as shown in Fig. 5(b).
  • the solution containing the polymer based composition comprising the antifouling-active filler according to the present invention is capable of significantly inhibiting the growth of the test bacteria in the broth solution compared to the solution containing polymer without antifouling- active filler (control sample).
  • the polymer based composition comprising the antifouling-active filler according to the present invention is capable of significantly inhibiting the growth of bacteria.
  • the immersion test of the sample of polymer based composition comprising different antifouling-active fillers according to the present invention was carried out by subjecting the sample polymer based composition to compression molding to obtain square polymer sheet. Said polymer sheet were then tested in the sea water to observe the fouling profile compared with the polymer sheet control sample as shown in Fig. 7.
  • test results show that extensive barnacles and algae fouling was found on the surface of the polymer sheet control sample (i.e. the polymer sheet without active filler) after 4 weeks while only slight fouling were found on the surface of most of the polymer sheet obtained from compressing the pellets of the polymer based composition comprising the antifouling-active filler according to the present invention. This shows the capability of the present invention in preventing aquatic fouling.
  • the polymer based composition having antifouling- active filler according to the present invention is a result of the components, particular amount of the components, process steps including other elements which yield the above advantages.
  • the antifouling polymer based composition according to the present invention is not limited to said components, particular amount of the components, process steps and elements detailed above. Modifications or variations can still be made to the present invention without departing from the scope and the spirit of the present invention.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne en particulier une composition à base de polymère antisalissure comprenant du polyéthylène (PE) et au moins une charge active antisalissure choisie dans le groupe composé de 2-méthylthio-4-éthylamino-6-tert-butylamino-s-triazine,2,4,4'-trichloro-2'-hydroxy diphényl éther, de 2-benzisothiazol-3-one, d'oxyde de zinc, de bis(2-pyridilthio) 1,1 '-dioxyde de zinc, d'hydroxyapatite dopée par un métal, de chitosane contenant du cuivre ou des mélanges de ceux-ci, la charge active antisalissure étant présente dans une plage allant de 0,1 à 5 parties en poids sur la base de 100 parties en poids de polyéthylène.
PCT/TH2016/000104 2015-12-24 2016-12-23 Composition à base de polymère anti-salissure WO2017111711A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TH1501007806 2015-12-24
TH1501007806A TH167832A (th) 2015-12-24 องค์ประกอบพอลิเมอร์ที่มีฤทธิ์ต้านการเกาะสะสมของสิ่งมีชีวิตที่เจริญเติบโตได้ในน้ำ

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WO2017111711A1 true WO2017111711A1 (fr) 2017-06-29

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Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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